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Mechanistic Studies of Rh(III)-Catalyzed C-H Olefination of Pyridines and Quinolines Promoted by Cu(OAc)2
ZHOU Jun,ZHANG Shuo-Qing,LI Bo,SHI Bing-Feng * #
Department of Chemistry, Zhejiang University, Hangzhou 310027, China
*Correspondence author
#Submitted by
Subject:
Funding: Specialized Research Fund for the Doctoral Program of Higher Education of China（No.20110101110005）
Opened online: 8 December 2015
Accepted by: none
Citation: ZHOU Jun,ZHANG Shuo-Qing,LI Bo.Mechanistic Studies of Rh(III)-Catalyzed C-H Olefination of Pyridines and Quinolines Promoted by Cu(OAc)2[OL]. [ 8 December 2015] http://en.paper.edu.cn/en_releasepaper/content/4665182
 
 
Detailed investigations towards the mechanistic studies of our previous work on Rh(III)-catalyzed C-H olefination of pyridines and quinolines are reported here. A working hypothesis was proposed for based on experimental and computional studies. The key reaction intermediate 11a was isolated and determined by X-ray crystallography, displaying a dimeric copper coordinated at the pyridine nitrogen. The KIE studies indicates that the cleavage of the C-H bond was not involved in the rate-determining step. The DFT calculations show the orientation of -CO- benefits its function as a directing group and promoted the following reaction. In addtion, controlled experiments have also been conducted. These studies indicate that Cu(OAc)2 might serve as both a convenient oxidant and Lewis acid.
Keywords:C-H olefination； rhodium； Lewis acid； pyridine；quinoline
 
 
 

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